


First (Last) Time

by brokencasbutt67



Series: Supernatural Kink Bingo 2019 [10]
Category: Supernatural
Genre: Apocalypse, F/M, First Time, Fluff, Reader Insert, Smut, Virgin Jack Kline
Language: English
Status: Completed
Published: 2019-01-22
Updated: 2019-01-22
Packaged: 2019-10-14 16:00:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,571
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17511611
Author URL: https://archiveofourown.org/users/brokencasbutt67/pseuds/brokencasbutt67
Summary: Kink: Your ChoiceSo for this I chose virginity. I'm not too comfortable writing Jack, I feel he's too young in relation to the show but he felt right as a character for this. Let me know what you think





	First (Last) Time

The apocalypse was happening. There was nothing to stop it, and there was nowhere to hide. The world as you know it will be destroyed. You look around the room at the abundance of hunters, some who you suspect may not even be hunters, but others who you have come to know and love, like Dean and Sam, Castiel and Gabriel, and Jack, despite how little you know of him. Tossing an empty beer can into the trash, you stand up and make your way out of the room, wanting to end the night on a high with your vibrator.

“(Y/N)!” Jack’s voice fills the corridor, a sense of nervousness filling it.  
“Hey Jack, ‘sup?” You asked, turning to face him.  
“I wanted to ask a favour…what with it being the last night and whatnot…you’re the only person I feel comfortable to share…this…with” He murmured, avoiding your eyes.  
“Sure, what’s up?” You asked, inviting him into your bedroom.  
“I uh…” He sighed, sitting beside you on the bed. It was in this moment that despite him being the same age as you, he looked so much younger.  
“I’m scared…I don’t wanna die…not how I am” He spoke, the last words coming out like venom.  
“What do you mean? There’s nothing wrong with you” You spoke softly, hand coming to hold one of his own.  
“Why am I a virgin then? Why doesn’t anyone wanna go near me” He spoke, his voice sounded so defeated, it made your heart break. You didn’t want to scare the kid off, but it killed you to see him so down. _Fuck it_ , you think, _the world’s ending, might as well tell him._

“I do” You said softly, meeting his eyes.  
“D-do you?” He stuttered, a nervousness that you recognised filled his voice.  
“I have for a while…I chose not to say anything because of the situation. We’re hunters after all, that’s a potential weakness that mon-fuck I’m rambling. Ignore me, what I’m saying is…there’s nothing wrong with you Jack. You’re funny, kind, caring, attractive and so much more that I just don’t know how to put into words” You spoke, cupping his cheeks.  
“And for what it’s worth, you don’t have to die a virgin” You uttered the last words, a nervousness filling your own voice.  
“W-what do you mean?” Jack asked, stuttering again.  
“We might as well go out on a bang” You chuckled lightly, smiling when Jack tilted his head in confusion.  
“We can make it a good night before we all…” You left the sentence ending open, not knowing what would happen to you all after tonight. Jack seemed to understand what you were saying though.  
“I admit, I do not know much about what to do” He admitted, cupping your hand in his own.  
“We take it slow and steady, don’t worry” You smiled. Jack nodded and shifted closer, until your thigh was pressed against his. Leaning over, you kissed him gently. You quickly learnt that Jack was responsive to touch, his body keened to the feather – like touches of your fingers against his skin, soft whimpers and moans rumbling from his throat. It didn’t take long for the pair of you to be laid, side by side, making out like a pair of horny teenagers. His hands seemed to move of their own accord, not that you minded, as he gripped your ass and shifted until you were laid on top of him. He groaned, voice deeper than you’d anticipated, and it turned you on too much. You could feel just how turned on Jack was too, his jeans were bulged beneath you.

Reaching down, you tugged your t-shirt over your head, tossing it aside, before reaching back and removing your bra, letting it fall to the floor. Jack groaned and shifted, tugging his own t-shirt off before tugging your chest down and latching his mouth onto your nipple, teasing the other with his thumb. You moaned and knotted your fingers through Jack’s hair, lightly tugging it. Jack moaned loudly, the vibrations racking through your body. Jack moaned and eventually pulled off. The ruffled mess of his hair suited him far too much.  
“Damn” You murmured, looking down to him. Reaching between your bodies, he unzipped his jeans, groaning at the relief. Climbing off of his lap, you tugged your own jeans away, before moving to close and lock the door. Jack smirked, too confident for it to be his first time.  
“D-do you have…the stuff?” He asked. You chuckled lightly.  
“You mean a condom?” You asked.  
“Yeah, that” He chuckled, clearly uncomfortable with talking about them.  
“No point in using one, we’ll be dead tomorrow anyway” You shrugged, but moved to open a drawer anyway.  
“I do have one though” You murmured. Jack smiled and stood up, moving to kiss you gently, while nudging his jeans down. You groaned and shifted, walking backwards to the bed. Bending backwards, you laid down on the bed while Jack knelt over you. His hands slid down your body, resting on your panties.  
“Are you sure?” He asked.  
“Yes, Jack, I’m sure” You promised. Jack smiled and pulled the panties down, tossing them aside. He kissed you, not bothering with subtleties any more. He trailed his hand to your thigh, and you could almost feel the nervousness setting in.  
“Want me to show you?” You asked. Jack nodded and shifted. You smiled and raised yourself on one elbow, using the other to guide his hand. You showed him just the right way to get your knees buckling, shouts leaving your throat. Jack smirked and watched intently as you came, gripping his wrist tightly. Jack smiled slightly when you finally came down from your orgasm.

Smirking up to you, Jack knelt between your legs. Despite it being his first time, he was eating you out like a pro. You’d barely recovered from your first orgasm when Jack was working you to a second, his tongue and fingers working in tandem to pull you closer. His blonde hair was teasing your thighs, your fingers longed to tug it and hold him against you, but you didn’t want to scare him. The knot in the pit of your belly was already wound tight, Jack’s tongue only tightened it until you came with a shout. Jack smiled as he sat back, clearly proud of himself for getting you to a second orgasm.  
“Holy fuck” You panted, hands flopped beside you.  
“Was that…okay? I let my human nature take over and I couldn’t stop it and-” Jack rambled, cut off when you kissed him deeply, the faint taste of you lingered on his tongue.  
“That was amazing” You smiled. Jack nodded and smiled, his innocence showing.  
“Swap places with me” You spoke, moving to stand up. Jack nodded and laid down, his black boxer shorts looked painfully tented. Reaching down, you tugged them off of his legs, letting them fall to the floor. Jack smiled up to you, his eyes fixated on your body. Picking up the condom, you moved to the bed and shifted to help him roll it on, chuckling slightly when his hips jerked against your hand. 

Shifting to climb back on the bed, you straddled his hips and kissed him gently, noses bumping. Jack’s hands moved to your hips. Reaching between your bodies, you lined up and guided Jack into you, moaning as you did. Your head fell back, mouth falling open. Gasps and moans left your throat as Jack moved deep inside of you. A loud moan left your throat as your ass hit his thighs. Jack seemed to be overwhelmed with pleasure, eyes wide and he looked so close to coming. You leant down and kissed him as you began to gyrate your hips, moving slow to let him become accustomed to the feeling. Condoms usually dulled the feeling of sex, for you, but with Jack, it was so much better. Maybe it wasn’t just the sex. Jack’s mouth moving to your neck dragged you from your thoughts as he nipped at your neck until you were tightening around him, coming with a shout for the third time. Shifting, you worked Jack to his first orgasm, and it didn’t take long. The condom swelled slightly as a shout left his throat, head flopping back against the pillow as his grip tightened on your hips.

Panting, you moved to climb off of Jack, removing the condom and knotting it before tossing it in the trash, while moving to grab some wipes to clean yourselves up slightly. When you returned, Jack was still panting, and he looked slightly lost.  
“You okay there, kiddo?” You asked, while wiping his skin.  
“Yeah…that was amazing” He breathed.  
“It’s sex, glad you had a good first time” You smiled, moving to lay beside him.  
“Was your first time good?” Jack asked, laid on his side to face you.  
“Not really, that’s why I didn’t particularly have an interest in sex for a long time” You shrugged. Jack frowned and cupped your cheek gently.  
“I’m sorry it wasn’t very good, if I had known…” He trailed off.  
“Don’t worry, I’ve moved on from it” You murmured, noting he seemed to be sleepy. Jack nodded and curled close to you, cuddling close together until you were both falling asleep, not wanting to be awake as the apocalypse occurred.


End file.
